Skip to content
  • Services
  • About Us
  • Our Team
  • Our Partnerships
    • Trusted Partners
    • Alive Partnership
  • Blog
Menu
  • Services
  • About Us
  • Our Team
  • Our Partnerships
    • Trusted Partners
    • Alive Partnership
  • Blog
CONTACT US
Linkedin

Baby Stepping in Decision Making

  • May 15, 2026
  • Matt Dickerson

Many leaders are seeking confidence in their direction and reassurance that their decisions are correct. It makes sense that they would want that feedback. It is also true that it can present a concern. The trouble comes when there is an assumption that clarity must exist before action can take place.

In other circumstances, professionals are seeking answers to questions about their careers, their next steps, and/or tough decisions about who to work with and for. If they can only think about it enough or do enough research, so they think, they can make the “right” decision.

Clarity Is Built Through Action

In reality though, clarity in decision-making is often built through action rather than found in advance. Waiting for complete certainty can delay progress.

Taking thoughtful action, even when things are not fully defined, creates useful data.

That data can then inform the next step.

I call these “baby-steps.”

The Origin of “Baby Steps”

In the early 1990’s, a movie came out called “What About Bob?”. Actor Bill Murray’s character, Bob Wiley, was a patient of the psychiatrist, Dr. Leo Marvin, played by Richard Dreyfus. Bob suffered from debilitating anxiety and goes to great lengths to maintain contact with his doctor, despite Dr. Marvin being on vacation. It is a funny enough movie. Anecdotally, I read somewhere that Dreyfuss legitimately did not care for Murray, and so their onscreen angst toward each other might be more about that than a demonstration of exceptional acting.

In the movie, Dr. Marvin encouraged Bob to take baby-steps through life. His encouragement was that by dividing what seemed to be insurmountable tasks into small steps, Bob could gather and propel himself forward through day-to-day life. (Or something along those lines; it has been quite some time since I last saw the movie!)

I see clients in similar situations when it comes to making decisions at work and in their careers. In both types of decision-making processes, they see the decision as binary. The answer is yes or no, do or do not, stay or leave, go for the promotion, or stay stuck forever, change careers or keep doing what they are doing in perpetuity.

Moving From Binary Thinking to Incremental Progress

If you are feeling unclear, it can be helpful to narrow the scope of the decision in front of you. Instead of focusing on long term strategy, consider what one step you can take this week. This reduces pressure and makes the work more tangible. It also creates an opportunity to learn.

A baby step!

Jian’s Career Crossroads

I was working with a senior leader in a large corporation. I will call him Jian. We had been meeting regularly for almost a year and in almost every session, he would find some way to bring the conversation back to the thing that was really on his mind.

He had established expertise in his field and had created a very successful career. But now he was considering a significant career pivot that would take him into an entirely different space.

While he had some of the prerequisite skill and knowledge, he did not know if he could be successful and he was not sure how satisfied he would be with the work.

So, he was stuck in binary thinking; stay or leave.

Breaking the Question Into Smaller Questions

Finally, in one session, I said to him, “You speak often about this possible transition into a career in another specialty. What kind of priority should we place on working through that in our time together?”

He acknowledged that it occupied a lot of thinking time and he was growing more and more frustrated about not knowing what to do about it.

I invited him to brainstorm the questions underneath the question. If he were to consider jumping to this new career what were smaller questions to which he did not know the answer?

Among those he produced, he recognized that he was not sure what he would have to do to upskill to meet the expectations of the role he coveted. He was aware of some transferable skills that he already possessed, but what was he missing?

I asked, “What would be the best way to find some answers to this question?”

“Well,” he said after thinking a minute, “I have a former colleague that has been doing this kind of work for a few years. I have not spoken with her in many years, but I bet she would be willing to fill in a few gaps for me.”

He had identified a baby step!

How Small Actions Create Momentum and Clarity

Each action can serve both as progress and as a source of information.

As you iterate an action in the direction you believe to be right, you are creating toward the goal that you think you want to obtain. You also become to some degree better informed on the situation and whether or not you want to keep going in your current direction.

In Jian’s case, he did engage his former colleague. She was able to answer a bunch of questions. Through that conversation, he learned that he would need to gain a new certification in order to even be equipped to apply for those kinds of roles.

Avoiding Premature Decisions Through Iteration

You probably can guess where our conversation went next: another binary “do or don’t” conundrum! How could he devise a next step that was smaller? We identified aspects of the certification that he lacked knowledge on. For example, it had been years since his colleague had gone through the certification. She could not answer basic questions about the cost or length of the certification process. Jian did not know what he would be signing up for if he moved forward with it.

Finding answers to those questions became his next baby step. He did some research on the institutions that offered this training and how they compared in commitment, flexibility of schedule, and cost.

Progress Without Premature Commitment

Notice that Jian is still far from making a decision on changing careers. He has not even decided to gain the new skills needed through certification. He believes, at this point, that saying yes to those things is likely to be the right decision for him. And he is taking actions to move toward that reality.

But what if he uncovered something he did not know about that kind of career change that was something he was not willing to sacrifice? Since he has not yet left his job or enrolled in that training, he has avoided making a mistake from which it would be difficult to recover. He would simply keep doing his current job in his current field with a newfound level of clarity and resolve.

From Certainty to Iteration

This approach requires a shift in mindset from being certain to being willing to iterate. It does not remove the need for thoughtful planning, but it reduces the expectation of perfection.

Individuals who can embrace iteration as a tool they regularly use usually find the answers they are looking for. Leaders who operate this way tend to create more engaged teams. They model adaptability and also an openness to feedback that can translate through the team.

If you are looking for clarity, consider what action would provide you with more information than you have today.

Take that step and observe the outcome.

Then, use what you learn to inform your next decision.

This is how clarity is built over time.

Do You Want to Build Clarity Over Time?

If you are navigating an important decision, feeling stuck between competing options, or looking for greater clarity in your leadership or career, I’d welcome the opportunity to continue the conversation.

  • Schedule a Call with Matt via Calendly
  • Email us at  matt@mattdickersonvalued.com
  • Connect on LinkedIn and start a conversation

No pressure—just a chance to explore how taking intentional next steps can help you gain clarity, move forward with confidence, and lead more effectively over time.

Share the post on your favorite platform

Facebook Twitter Linkedin Wordpress

EMAIL NEWSLETTER SIGN UP

Join the Coaching for Clarity newsletter to receive thoughtful guidance, practical tools, and a dose of encouragement—right to your inbox.

EXplore more posts

Reframing Subject Matter Expertise

High-performing professionals often encounter an important shift when moving into leadership roles, where success is no longer defined by doing the work themselves but by developing others to do it well.

Coaching and Development

What Strong Leaders Do Differently: The Courage to Lead

Leadership isn’t defined by title—it’s revealed through the courage to develop others. Explore how coaching, mentorship, and prioritizing people can amplify your impact and define you as a true leader.

People Management

What Makes Effective Coaching: Desire, Context, and Identity

People often ask whether they should get a coach when they reach a crossroads, face a challenge, or experience interpersonal friction at work. But coaching is only effective when the conditions are right. Explore when coaching works, when it doesn’t, and why timing matters.

Coaching and Development

Previous Page1 Page2 Page3 Page4 Page5 Next

Let's continue
the conversation

We would love to chat with you about the season that you or your team find yourselves in. Here's how we can we keep the conversation going.

Schedule a Call

Use Calendly to find a time to connect with Coaching for Clarity's founder, Matt Dickerson.

Email Us

Send an email to: matt@mattdickersonvalued.com

connect on linkedin

Follow and connect with Matt.

Linkedin
  • Services
  • About Us
  • Our Team
  • Contact
Menu
  • Services
  • About Us
  • Our Team
  • Contact
return to top

© 2026 Coaching for Clarity

Designed by Elevate Online

Privacy Policy